Perfume composition

ABSTRACT

A new compound, 2-(1&#39;&#39; -hydroxymethyl - ethyl) -5- methyl-5-vinyl - tetrahydrofuran has been discovered in an essential oil of a lilac flower. This compound consists of four steroisomers and is useful as an ingredient to be incorporated in floral perfumes. This compound is obtained by selectively reducing the formyl radical of 2- (1&#39;&#39; formylethyl) -5- methyl-5- vinyl tetrahydrofuran.

United States Patent [191 Wakayama et al.

[ Oct. 9, 1973 [30] Foreign Application Priority Data Aug. 29, 1970 Japan 45/75838 [52] US. Cl. 252/522, 260/347.8 [51] Int. Cl ..C11b 9/00 [58] Field of Search 252/522; 260/347.8

[56] References Cited UNITED STATES PATENTS 3,227,731 1/1966 Kulka 252/522 X 3,668,134 6/1972 Lamberti et al. 252/522 X Primary Examiner-Albert T. Meyers Assistant ExaminerFrederick E. Waddell Att0rneyLane, Aitken, Dunner & Zi ems [57] ABSTRACT A new compound, 2-(1 -hydroxymethyl ethyl) -5- methyl-S-vinyl tetrahydrofuran has been discovered in an essential oil of a lilac flower. This compound consists of four steroisomers and is useful as an ingredient to be incorporated in floral perfumes. This compound is obtained by selectively reducing the formyl radical of 2- (1' formylethyl) -5- methyl-S- vinyl -tetrahydrofuran.

3 Claims, No Drawings l PERFUME COMPOSITION This invention relates to a new compound, 2-( I '-hydroxymethyl)-5-methyl -5-vinyltetrahydrofuran.

A new compound which is useful as a perfume ingredient has been discovered in a alcoholic section of an essential oil of a lilac flower. The compound is 2 (l' -hydroxylmethyl -ethyl) -5- methyl-S-vinyltetrahydrofuran having the following formula:

' "'HOH0 J J CH \O J9. ps

Accordingly, an object of the present invention is to provide a new compound useful as a perfume ingredi- CHI.

The new compound, 2-( l -hydro'xymethyl-ethyl) -5- methyl -5-vinyl-tetrahydrofuran, having the above formula, has four stereoisomers. It is very difficult to separate these isomers, since they extremely close to each other, therefore, the perfume value of each individual isomer has not been confirmed as yet. However, a mixture of the four isomers has value as a perfume.

Therefore the compound, 2-(1' -hydroxymethylethyl)-5-methyl-5-vinyltetrahydrofuran of the present invention is a mixture of the four isomers.

Since the above compound has been discovered in the essential oil of a lilac flower, the compound has been named lilac alcohol" which name will be used hereinafter.

When the lilac alcohol is used as an ingredient for various floral perfumes, it gives a very good fragrance. In other words, this lilac alcohol harmonizes well with other odoriferous compounds; thus being useful in the preparation of a great variety of perfume compositions.

In addition, because of the strong fixative property of the lilac alcohol, a perfume composition containing this lilac alcohol retains-advantageously harmonized floral odors for a considerably long period of time.

Accordingly, this lilac alcohol may be advantageously used to prepare various perfume compositions, and the amount may be varied within a wide range,

preferably to l5 percent by weight.

The lilac alcohol of the present invention can be produced by selectively reducing the formyl radical of 2- l '-formyl-ethyl)-5-methyl-5-vinyl-tetrahydrofuran having the following formula:

t CH=CHI The compound having the above formula is known to 'the art and a process for its production is disclosed in P. Naegel and G. Weber, Tetrahedron Letters, No. 12, pages 959 to 962 (1970). 7

Reducing agents, suitable for selectively reducing the formyl radical of the compound shown in the above formula, include sodium borohydride, lithium aluminum hydride, and lithium borohydride. The Meermein- Ponndorf reduction process which employs aluminum alcoholate as the reducing agent may'also be used.

The gas chromatographic analysis of the lilac alcohol obtained by the above-described processes proves that the lilac alcohol so produced consists of a mixture of four isomers, the same as those found in the essential EXAMPLE 1 6.7 grams (0.04 mols) of 2-( l'- formyl -ethyl)-5- methyl -5-vinyl -tetrahydrofuran was dissolved in 10 ml of methanol. Then, the solution thus prepared was added dropwise to 40 ml of a methanol solution containing 1.5 grams of sodium barohydride while agitat ing. The reaction was carried out at a temperature of below 35C for two hours. The remaining sodium borohydride was decomposed with acetoneand the reaction mixture was then added to ice water. The oil components were then extracted with ether which was then distilled off to give a reaction product of 7.1 grams. This product was fractionated, yielding 5.9 grams of lilac alcohol. The product was found to possess the following properties:

Boiling point 1l3-l l5C/12 mmI-Ig, d '-=O.9778, n,, =l.455l, Spectrum absorption at IR=vmM 3520 cm, 3,08'0', 1540390, "926 "cm", I l'l'Of l' ,OTO EEH The above properties indicate that this product includes alcohol and vinyl radicals and ether linkage.

Analysis for C l-I O Calculated values (percent) C=70.59, I-I=l0.59

Found values (percent) C- -70.30, H=10.72

EXAMPLE 2 6.7 gram 0.04 mols) of 2- 1'- formyl ethyl) -5- methyl-S- vinyltetrahydrofuran was dissolved in 50 ml of anhydrous isopropyl alcohol. The solution thus prepared was added to 20 ml of an anhydrous isopropyl alcohol solution of aluminum isopropoxide (3 grams). This mixture was boiled in an oil bath and the acetone formed during the reaction was distilled off. The reac tion was continued for 2 hours. Upon completion of the reaction, 500 ml of water was added dropwise therein so as to decompose the excess aluminum isopropoxide. 20 ml of 5 percent sulfuric acid was then added to dissolve the aluminum hydroxide and the reaction product was extracted with ether. After the ether was distilled off, the resulting extract was fractionally distilled atv l l3-l l5C/l2 mmHg to obtain 6 grams of the desired of fraction. The product thus obtained was found to be lilac alcohol having same properties as that obtained in Example 1.

Perfume compositions including the lilac alcohol ob tained in Examples 1 and 2 as a ingredient are shown below. (The perfume compositions of Examples 3-6 were prepared by blending the ingredients using a conventional blending process.)

EXAMPLE 3 Ingredients Parts by Weight Lilac type perfume composition Lilac alcohol 15 Phenylethyl alcohol 25 Benzylacetate l0 Aubepine 6 Cinnamic alcohol IO Corolla] 30 Iso-eugcnol l Amylcinnamic aldehyde 3 Total EXAMPLE 4 A chypre perfume composition Lilac alcohol Bergamot Oil Benzylacetate Linalool Dihydrojasmone. 10% in bcnzyl alcohol Phenylcthyl alcohol Gamma-methyl ionone lso-eugenol Santalex T Oakmoss absolute Vetiverol Heliotropine Coumarine Musk ketone Musk ambrette v Vanillin Total EXAMPLE 5 Lilac type perfume composition: Lilac alcohol Phenylethyl alcohol Benzyl acetate Aubepine Cinnamic alcohol Cyclamene aldehyde Coronal- Linalool Laurinal Heliotropine lso-eugenol Terpineol Courmarine Total EXAMPLE 6 Fo'urgere perfume composition 1 Lilac alcohol Lavender oil Linalyl acetate lOO Methyl ionone 10 Patchouli oil 10 Oakmoss absolule l0 Bergamot oil 150 Geraniol 20 Dihydrojasmone, 1% in benzyl alcohol 20 Vetiverol 20 Phenylethyl alcohol l5 Musk ketone 50 Coumarine Vanillin 15 Total i000 The perfume composition of Examples 3-6 were 77 found to have a better balanced fragrance and a more natural and more pleasent floral note than a composition containing no lilac alcohol. The fragrance was retained longer than compositions containing no lilac alcohol.

What is claimed is l. A perfume composition comprising a fragrance imparting amount of 2-( l 'hydroxymethyl-ethyl)-5- methyl-5-vinyl-tetrahydrofuran and at least one other odorferous compound.

2. The perfume composition of claim 1 wherein the amount of said 2-( l'hydroxymethyl-ethyl)-5-methyl-5- vinyl-tetrahydrofuran present is within the range of from 10 percent to 40 percent by weight of said composition.

3. The perfume composition of claim 1 wherein the amount of said 2-( l 'hydroxymethyl-ethyl)-5-methyl-5- vinyl-tetrahydrofuran present is within the range of from 10 percent tol5 percent by weight of said composition. 

2. The perfume composition of claim 1 wherein the amount of said 2-(1''hydroxymethyl-ethyl)-5-methyl-5-vinyl-tetrahydrofuran present is within the range of from 10 percent to 40 percent by weight of said composition.
 3. The perfume composition of claim 1 wherein the amount of said 2-(1''hydroxymethyl-ethyl)-5-methyl-5-vinyl-tetrahydrofuran present is within the range of from 10 percent to 15 percent by weight of said composition. 